Reaktion #59518

Reaktionsgleichung

3-(4-methoxyphenyl)-2-phenylpropionic acid

Thionylchloride

→

6-Methoxy-2-phenylindan-1-one

Ausbeute 67.8%

Lösungsmittel

methylenechloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigereaction mixture
2. 2
   SonstigeSolvent was evaporated under vacuum
3. 3
   workup.DISSOLUTIONPrecipitate was dissolved to methylenechloride
4. 4
   TemperaturSolution was cooled to 0-3° C
5. 5
   workup.ADDITIONThis solution and aluminium chloride (2.5g) were mixed slowly over 4 hours
6. 6
   Sonstigeunder 4° C
7. 7
   workup.ADDITIONAfter mixing
8. 8
   Sonstigereaction mixture
9. 9
   workup.STIRRINGwas stirred at room temperature for 2 h
10. 10
    SonstigeReaction
11. 11
    Sonstigewas quenched
12. 12
    workup.ADDITIONby pouring to dilute ice cold hydrochloric acid
13. 13
    SonstigeLayers were separated
14. 14
    Extraktionwater solution was extracted with methylenechloride
15. 15
    WaschenCombined organic layers were washed with water
16. 16
    Sonstigedried
17. 17
    Sonstigeevaporated
18. 18
    SonstigeCrude product was triturated

Vorschrift

To solution of 3-(4-methoxyphenyl)-2-phenylpropionic acid (4.6 g) in dry methylenechloride (26 ml) was added two drops of dry DMF. Thionylchloride (3 ml) was added and reaction mixture was stirred at 40° C. for 4 h. Solvent was evaporated under vacuum. Precipitate was dissolved to methylenechloride. Solution was cooled to 0-3° C. This solution and aluminium chloride (2.5g) were mixed slowly over 4 hours keeping temperature under 4° C. After mixing reaction mixture was stirred at room temperature for 2 h. Reaction was quenched by pouring to dilute ice cold hydrochloric acid. Layers were separated and water solution was extracted with methylenechloride. Combined organic layers were washed with water, dried and evaporated. Crude product was triturated to give 2.9 g of 6-Methoxy-2-phenylindan-1-one. 1H-NMR (400 MHz, d6-DMSO): 7.56 (d, 1H), 7.35-7.23 (m, 4H), 7.18-7.13 (m, 3H), 4.02 (dd, 1H, J 3.9, 8.0 Hz), 3.82 (s, 3H), 3.61 (dd, 1H, J 8.0, 17.2 Hz), 3.11 (dd, 1H, J 3.9, 17.2 Hz).

Quelle